2-(2-methoxy-3-oxoisoindol-1-yl)-1-phenylethanone | 1333433-41-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-methoxy-3-oxoisoindol-1-yl)-1-phenylethanone
• 英文别名: N-methoxy-3-(2-oxo2-phenylethyl)isoindolin-1-one
• CAS: 1333433-41-2
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: CGLHHZKCGLFMEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(2-methoxy-3-oxoisoindol-1-yl)-1-phenylethanone 在 potassium hydroxide 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Regioselective Condensation of Alkylidenephosphoranes to N-Methoxy- and N-Anilino-1H isoindole-1,3-(2H)-diones

  摘要：

  Treatment of 2-methoxyisoindoline-1,3-dione with resonance-stabilized alkylidenephosphoranes afforded the corresponding monoalkenes as the sole reaction product, in similar to 58-63% yields, whereas more than 80% yields of the same monoolefin products were obtained when the reactions were carried out under microwave conditions. Similarly, 2-(phenylamino)isoindoline-1,3-dione reacted under either thermal or microwave conditions to give only the corresponding monoalkene derivatives. The alkene products from both substrates were further reduced to the corresponding isoindoles using Zn-dust in EtOH. Prediction of the designed compounds and the in vivo anti-inflammation activity of the products in the rat adjuvant model were also studied. The work is the first demonstration of the anti-inflammatory activity of phthalimide derivatives.

  DOI：

  10.1080/00397911.2010.551170
• 作为产物：
  描述：

  N-甲氧基邻苯二甲酰亚胺 在 ammonium acetate 、 锌 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 0.2h， 生成 2-(2-methoxy-3-oxoisoindol-1-yl)-1-phenylethanone
  参考文献：
  名称：

  Regioselective Condensation of Alkylidenephosphoranes to N-Methoxy- and N-Anilino-1H isoindole-1,3-(2H)-diones

  摘要：

  Treatment of 2-methoxyisoindoline-1,3-dione with resonance-stabilized alkylidenephosphoranes afforded the corresponding monoalkenes as the sole reaction product, in similar to 58-63% yields, whereas more than 80% yields of the same monoolefin products were obtained when the reactions were carried out under microwave conditions. Similarly, 2-(phenylamino)isoindoline-1,3-dione reacted under either thermal or microwave conditions to give only the corresponding monoalkene derivatives. The alkene products from both substrates were further reduced to the corresponding isoindoles using Zn-dust in EtOH. Prediction of the designed compounds and the in vivo anti-inflammation activity of the products in the rat adjuvant model were also studied. The work is the first demonstration of the anti-inflammatory activity of phthalimide derivatives.

  DOI：

  10.1080/00397911.2010.551170

文献信息

• New Heteroannulation Reactions of <i>N</i>-Alkoxybenzamides by Pd(II) Catalyzed C–H Activation
  作者：Joe W. Wrigglesworth、Brian Cox、Guy C. Lloyd-Jones、Kevin I. Booker-Milburn

  DOI：10.1021/ol202187h

  日期：2011.10.7

  through a highly efficient and E-selective C–H activation/Heck/Aza-Wacker sequence. Substoichiometric amounts of benzoquinone can be employed in a cooperative oxidation system with O2, leading to facile purification of products. Modification of the reaction conditions provides a general route to substituted phthalimides by carbonylation with CO. Both systems were found to tolerate a wide range of functionality

  提出了一种新的钯（II）催化方法，用于从N-烷氧基苯甲酰胺直接合成亚烷基异吲哚满酮。异吲哚啉酮的形成通过高效的E选择性C–H活化/ Heck / Aza-Wacker序列进行。亚化学计量的苯醌可以与O 2一起在协同氧化系统中使用，从而可以轻松纯化产物。反应条件的改变为通过CO羰基化取代苯二甲酰亚胺提供了一条通用途径。发现这两种体系都可以耐受广泛的功能。